Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2011-05-10
2011-05-10
Chandrakumar, Nizal S (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
07939679
ABSTRACT:
Disclosed is a method for total synthesis of CTX1B, which is developed for the synthesis of a ciguatoxin analogue such as CTX3C and enables the more efficient application of an established reaction to the total synthesis of CTC1B. More specifically, disclosed is a method for total synthesis of CTX1B comprising; an O.S-acetal formation for synthesizing a novel compound (3); a radical cyclization reaction for constructing a 9-membered ring formation reaction including a novel compound (6) through a novel compound (8) and yielding a compound (D); and a deprotection for yielding CTX1B. Also disclosed are novel compounds (1) to (8) which are particularly useful for synthesis of CTX1B and can be used for the synthesis of a ciguatoxin analogue.
REFERENCES:
“A concise route to the right wing of ciguatoxin”, Tatami et al., Tetrahedron Letters 44 (2003), p. 5229-5233.
“Synthesis of the Fully Functionalized ABCDE Ring Moiety of Ciguatoxin”, Kobayashi et al., Organic Letters, 2004, vol. 6, No. 5, p. 751-754.
“Total Synthesis of Ciguatoxin and 51-HydroxyCTX3C”, Inoue et al., J. Am. Chem. Soc. 2005, 128, p. 9352-9354.
“First- and second-generation total synthesis of ciguatoxin CTX3C”, Inoue et al., PNAS, Aug. 17, 2004, vol. 101, No. 33, p. 12013-12018.
“Synthesis-Based Approach toward Direct Sandwich Immunoassay for Ciguatoxin CTX3C”, Oguri et al., J. Am. Chem. Soc., 2003, 125, p. 7608-7612.
“A New Stereoselective Synthesis of Ciguatoxin Right Wing Fragments”, Inoue et al., J. Org. Chem. 2004, 69, p. 2797-2804.
Supplemental European Search Report (SESR) for corresponding Application No. EP 07706872.4-2101/1982988, PCT/JP2007050545 (Mar. 11, 2010).
M. Hirama et al.: “Total Synthesis of Ciguatoxin CTX3C,” Science, vol. 294, pp. 1904-1907, 2001 (Washington, DC, USA), XP002572475, Figures 1-3 (Cited in SESR).
Hirama Masahiro
Inoue Masayuki
Chandrakumar Nizal S
Hahn Roger C.
Hahn & Voight PLLC
Japan Science & Technology Agency
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